Brown azo dyestuff and process of making same.



No Drawing.

; TTED STATEg PATENT @FFTQE FRANZ SCHOLL AND WILLY TROPP,OF-HGCHST-ON-THE-MAIN, GERMANY, .ASSIG'NORS TO EARBWERKE VORM. MEISTERLUCIUS GEEMANY, A CORPOR ATION OF GERMANY.

& BRUNING, OF HtjCI-IST-ON-THE-MAIN,

- BROWN'AZO DYESTUFF AND PROCESS OF MAKING SAME.

both residing at-Htichst-on-the-Main, Ger-' many, have invented certainnew and useful Improvements in Brown Azo Dyestutf and Processes ofMaking Same, of which the following is a specification.

- wherein R stands for the residue of an' Y aromatic sulfonic acid,and.X for an We have foundthat fast brown acid dyestufis, dyeing veryevenly, are produced by causing the diazo compounds ofm-amino-yarylaziminobenzenesulfonicacids to act upon theQ-arylamino-S-oxynaphthalene-G- sultonic acids. The a-zo-dyestutts thusobtained have the constitution:

aryl residue. These dyestufi's are brown powders, readily soluble inwater to a brown solution which scarcely changes on addition of ammonia,and on addition of a mineral acid'assumes a slightly greenish color.They dissolve in conceiitrated sulfuric acid with a pure red color, butare insoluble in alcohol, ether and ligroin. The dyestufi's dye Wool inan acid bath reddish-brown to brown tints. Them-amino-Y-arylaziminobenzenesulfonic acids are obtained from thepartlyreduced products resuItingtrOm the reaction of2.-t-dinitrochloizobenzene upon aromatic aminosult'onic acids with theaid of nitrous acid and subsequent reduction.

i The following examples illustrate our invention:

1. 81 kilos of the sodium salt of the in amino y msulfophenylaznninobenzene are dissolved with 7 kilos of sodium nitritein about GOOlitersot water and this solution is introduced at 30-40 G.into 30 kilos of hydrochloric acid of 19 B. which has been diluted withwater so as to give about .150 liters. This mixture is stirred for sometime. When the diazotation is completed,

Specification of Letters Patent.

Application filed 0ctober 6, 1911.

Patented Nov. l 2, 19172. Serial No. 653,288.

l the diazo compound is introduced into a solution .of 34 kilos ofQ-p-tolylaniino-S- oxynaphthalene-6-sulfonic acid and 525 kilos ofcalcined soda in about 600 liters of water. The brown dyestuif solution,which immediately forms, is gently heated for some further hours, andafter addition of common salt stirred for a good time. The separatedproduct is then filtered oft and dried. The constitutional formula ofthis dyestufi. is as It is a brown powder, readily soluble in Water toabrown solution which on addition of a 'mineral acid becomes slightlygreenish, and on addition of caustic soda lye slightly reddish, scarcelychanging by the addition of ammonia. In concentrated sulfuric acid itdissolves with a. fuchsinered color and is insoluble in alcohol, etherand lig'roin. lt dyes wool in an acid bath brown tints.

34- kilos of the sodium salt of the m-ami1m-7-5-su]to 1naphthylaziminoben- Zeno are dissolvcdjn water, mixed with 7 kilos ofsodium nitrite and run at 35et0 into 30 kilos of hydrochloric acid of 19Bel which has been diluted with water so as to giyenbout 200 liters.'A't'ter stirring the 95 mixture for several hours the diazotatioir-iscomplete and the diazo compound, which is ditlicultlv soluble, separatesin crystais. This (.0lll]) 1l-.]ll(l is then introduced into a solutionof 34 kilos of sodium salt of il-phenylan1ino-t oXynaphthalene-t-sulfonic acid and kilos of calcined soda in about 600 liters of Water,whereupon the dyestufi' immediately separates in the form of brownflakes. After some hours the mixture is heated to about and on coolingfiltered dyestuffs of the constitution:

0E and dried. The dyestufi? thus obtained has the constitutionalformula:

l l SO Na some i SOINEL/ wherein .7 stands for an aromatic sultonic acidand X for an aryl residue; being brown powder, soluble in water with abrown color, scarcely changing on addition of ammonia, turning slightlygreenish on addition of a mineral acid, dissolving in concentratedsulfuric acid with a pure rcd color, being insoluble'in alcohol, otherand ligroin, and dyeing wool reddish-brown to brown tints.

2. As a new article of manufacture, the

dyestufl' of the constitution:

being a brown powder, readily soluble in water with a brown color,turning slightly greenish on addition of a mineral acid and on additionof caustic soda lye slightly reddish, scarcely changing on'addition ofammonia, dissolving in concentrated sulfuric acid with afuchsine-redcolor-,insoluble in alcohol, ether and ligroin and dyeing'wool browntints.

3, The process of manufacturing brown mono-azo dyestuffs, which consistsin cansing the diazo compounds of the m-aminoarylaziminobenzolsulfonicacids to act upon ary-Q-amino 8 oxynaphthalene-dsulfonic ac1 tures inpresence of two witnesses.

" FRANZ SCHOLL:v lWILLY TROPP.

iiitnesses: i

JEAN GRUND, CARL GRUND.

Inn-testimony whereof, we aflix our signa-

